Compound

(8S,9R)-epoxy-(5Z,11Z,14Z)-eicosatrienoate

An 8,9-EET(1−) that is the conjugate base of (8S,9R)-EET, obtained by deprotonation of the carboxy group; major species at pH 7.3.

Definition from ChEBI (CHEBI:131974), read 2026-09-23. CC BY 4.0.

CHEBI:131974ChEBI

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Structure

2D depiction · 3D model shown

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A generated conformer of (8S,9R)-epoxy-(5Z,11Z,14Z)-eicosatrienoate — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound, anion
Formula: C20H31O3
Mass: 319.465 g/mol
Charge: -1
InChIKey: DBWQSCSXHFNTMO-ZZMPYBMWSA-M
SMILES: CCCCC/C=CC/C=CC[C@H]1O[C@H]1C/C=CCCCC(=O)[O-]
Look it up: ChEBI PubChem By InChIKey

Identity from ChEBI, geometry from PubChem. Not evidence.

What it touches on the way

Mechanistic reach

2 entities

2 entities reached.

0 reported hops2 assembled from the scaffold

What the reference databases state

Chemical structure

(8S,9R)-epoxy-(5Z,11Z,14Z)-eicosatrienoate is the enantiomer of (8R,9S)-epoxy-(5Z,11Z,14Z)-eicosatrienoateCompoundChEBI CHEBI:131974Inferred only

Statements

2 statements

2 statements · 1 reference database · Subject: (8S,9R)-epoxy-(5Z,11Z,14Z)-eicosatrienoate · Sources: Rhea

Order

(8S,9R)-epoxy-(5Z,11Z,14Z)-eicosatrienoate is metabolised by CYP2C9ProteinRhea RHEA:49928Inferred only
(8S,9R)-epoxy-(5Z,11Z,14Z)-eicosatrienoate is metabolised by CYP2J2ProteinRhea RHEA:49928Inferred only

Reactions

3 reactions

(5Z,8Z,11Z,14Z)-eicosatetraenoate+reduced [NADPH--hemoprotein reductase]+dioxygen(8S,9R)-epoxy-(5Z,11Z,14Z)-eicosatrienoate+oxidized [NADPH--hemoprotein reductase]+water+hydron
Catalysed by CYP2C9 or CYP2J2
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:49928CC BY 4.0Reference data
(8S,9R)-epoxy-(5Z,11Z,14Z)-eicosatrienoate+waterCHEBI:138002
Catalysed by EPHX2
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:53972CC BY 4.0Reference data
(8S,9R)-epoxy-(5Z,11Z,14Z)-eicosatrienoate+waterCHEBI:138008
Catalysed by EPHX2
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:54016CC BY 4.0Reference data

Other names

8 names

Resolves to: (8S,9R)-epoxy-(5Z,11Z,14Z)-eicosatrienoate

Also called: (8S,9R)-Ep-(5Z,11Z,14Z)-ETrE(8S,9R)-EpETrE(8S,9R)-EpETrE(1-)(8S,9R)-EpETrE(1−)(8S,9R)-epoxy-(5Z,11Z,14Z)-icosatrienoate8(S),9(R)-EET(1-)8(S),9(R)-EET(1−)
Systematic name: (5Z)-7-{(2S,3R)-3-[(2Z,5Z)-undeca-2,5-dien-1-yl]oxiran-2-yl}hept-5-enoate